Episode 793 | TinySeed Tales s5e3: Building Momentum

Episode 793 | TinySeed Tales s5e3: Building Momentum

Author: Rob Walling September 4, 2025 Duration: 27:16
What happens when momentum hits and your biggest challenge becomes keeping up? In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus. Topics we cover:  (1:40) – Closing his biggest deal ever and what it unlocked (4:26) – Learning how to do enterprise sales (6:20) – How SOC 2 made the product stronger (12:18) – New hires are paying off (18:23) – Building the Salesforce integration (22:13) – Getting pull from the market, not pushing (24:10) – Taking customers from unicorns  Links from the Show:  TinySeed SaaS Accelerator - Applications close on September 9th Coaching Call Bonus Invest in TinySeed YNAB (You Need A Budget) Dynamite Jobs OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

Rob Walling hosts Startups For the Rest of Us, a long-running conversation focused squarely on the realities of building a company without massive venture funding. This isn't about Silicon Valley fairy tales; it's a practical, ground-level view of entrepreneurship. Each episode delves into the specific journeys of founders who are starting, acquiring, or growing their SaaS businesses, emphasizing the path of bootstrapping. You'll hear the unvarnished details-the strategic decisions, the unexpected obstacles, and the hard-won victories that define the daily life of a founder. The discussions are built on real stories, offering tangible lessons from both struggle and success. For anyone who has ever felt that the typical startup narrative doesn't reflect their own resource-constrained reality, this podcast provides a necessary and relatable perspective. It’s a deep resource for actionable advice and genuine camaraderie, connecting you with the experiences of those navigating the same challenging terrain. Tune in for honest conversations that cut through the hype and focus on building sustainable businesses.
Author: Language: en-us Episodes: 100

Startups For the Rest of Us
Podcast Episodes
Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead" [not-audio_url] [/not-audio_url]

Duration: 37:48
How do you know it’s time to move on from a product that’s growing? In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching…
Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom [not-audio_url] [/not-audio_url]

Duration: 31:26
What’s the real roadmap to lasting financial freedom? In this episode, Rob Walling chats with Nick Maggiulli about his new book, The Wealth Ladder. Nick explains how to identify your current financial stage and what it r…
Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions [not-audio_url] [/not-audio_url]

Duration: 27:46
Looking back on your entrepreneurship journey, which decisions made the biggest impact? In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learni…
Episode 779 | 10 Myths Most SaaS Founders Believe [not-audio_url] [/not-audio_url]

Duration: 44:32
Are common SaaS myths sabotaging your success? In this episode, Rob Walling sits down with SaaS growth expert (and TinySeed Institute coach) Marc Thomas to break down ten persistent and damaging myths believed by many Sa…